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These ions have also been observed to exhibit anion\u2013\u03c0 interaction tendencies of interest in molecular recognition applications. The benefits of phosphonium incorporation, however, have not yet been extended to the smallest benzene diimides. Here, we report that dibrominated pyromellitic diimide and mellophanic diimide both readily undergo substitution reactions with phosphine sources to yield bisphosphonium compounds. In the single crystalline form, these dications display anion\u2010\u03c0 interactions and, in the case of mellophanic diimide, the stabilization of a bromide\u2013water H\u2212bonding ring pattern. The reaction of these dications with chemical reductants readily provides the singly and doubly reduced redox states, which were characterized by UV\u2010vis spectroscopy and found to exhibit intense absorptions extending into the near\u2010IR region. Taken together, this work demonstrates that phosphonium incorporation onto congested aromatic diimide scaffolds is synthetically viable and produces unusual electron\u2010poor compounds.<\/jats:p>","DOI":"10.1002\/chem.202402791","type":"journal-article","created":{"date-parts":[[2024,7,30]],"date-time":"2024-07-30T11:44:14Z","timestamp":1722339854000},"update-policy":"https:\/\/doi.org\/10.1002\/crossmark_policy","source":"Crossref","is-referenced-by-count":3,"title":["Bisphosphonium Benzene Diimides"],"prefix":"10.1002","volume":"30","author":[{"given":"Feven","family":"Leake Gebresilassie","sequence":"first","affiliation":[{"name":"Chemistry Department Macalester College  1600 Grand Avenue Saint Paul, MN 55105 USA"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Min","family":"Ji Kim","sequence":"additional","affiliation":[{"name":"Chemistry Department Macalester College  1600 Grand Avenue Saint Paul, MN 55105 USA"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Daniela","family":"Castellanos","sequence":"additional","affiliation":[{"name":"Chemistry Department Macalester College  1600 Grand Avenue Saint Paul, MN 55105 USA"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Conor H.","family":"Broderick","sequence":"additional","affiliation":[{"name":"Chemistry Department Macalester College  1600 Grand Avenue Saint Paul, MN 55105 USA"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Steven M.","family":"Ngo","sequence":"additional","affiliation":[{"name":"Chemistry Department Macalester College  1600 Grand Avenue Saint Paul, MN 55105 USA"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"suffix":"Jr.","given":"Victor G.","family":"Young","sequence":"additional","affiliation":[{"name":"Department of Chemistry University of Minnesota  207 Pleasant St. S.E. 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